| Identification | Back Directory | [Name]
Levothyroxine sodium | [CAS]
55-03-8 | [Synonyms]
Levothyroxine Sdium
Levothyroxine sodium
Levothyroxine sodium ,T4
L-ThyroxineSodiumSaltB.P.
L-THYROXINE SODIUM ANHYDROUS
L-THYROXINE SODIUM PENTAHYDRATE
L-THYROXINE SODIUM SALT PENTAHYDRATE
Sodium 4-O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine
3-Amino-4-(4-(4-OH-3,5-diiodophenoxy)-3,5-diiodophenyl))but.ac.Na salt
L-Tyrosine,O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-, sodiuM salt (1:1)
3-[4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL]-L-ALANINE PENTAHYDRATE
sodium (s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propionate
sodiuM (S)-2-aMino-3-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)propanoate
(S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propionic Acid odium
3-[4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL]-L-ALANINE SODIUM SALT PENTAHYDRATE
(s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propionic acid sodium salt
SODIUM (S)-2-AMINO-3-[4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL]PROPIONATE PENTAHYDRATE
(S)-2-AMINO-3-[4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL]PROPIONIC ACID SODIUM SALT PENTAHYDRATE
(S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propionic Acid Sodium Salt
Sodium (S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propionate | [EINECS(EC#)]
200-221-4 | [Molecular Formula]
C15H20I4NNaO9 | [MDL Number]
MFCD00149110 | [MOL File]
55-03-8.mol | [Molecular Weight]
888.93 |
| Chemical Properties | Back Directory | [Melting point ]
207-210 (dec.)(lit.)
| [alpha ]
D20 -4.4° (c = 3 in 70% ethanol) | [density ]
d420 2.381 | [storage temp. ]
2-8°C
| [solubility ]
cell culture medium: 0.1 mg/mL
| [form ]
powder
| [color ]
Off-white to light yellow | [BCS Class]
1,3 | [Stability:]
Hygroscopic | [InChI]
InChI=1/C15H11I4NO4.Na.H/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23;;/h1-2,4-5,12,21H,3,20H2,(H,22,23);;/t12-;;/s3 | [InChIKey]
JMHCCAYJTTWMCX-QWPJCUCISA-M | [SMILES]
O(C1C(=CC(C[C@H](N)C(=O)O)=CC=1I)I)C1C=C(I)C(O)=C(I)C=1.[NaH] |&1:6,r| | [EPA Substance Registry System]
L-Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-, monosodium salt(55-03-8) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Usage]
One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroid hormone, but has been used to treat hyperlipidemia. | [Originator]
Synthroid,Flint,US,1953 | [History]
On August 14, 1997, the FDA declared levothyroxine sodium tablets a “new drug.” On February 15, 2017, the FDA approved levothyroxine sodium (brand name: Tirosint-SOL, developed by IBSA Pharma Inc.) oral solution for hypothyroidism and pituitary thyroid-stimulating hormone (TSH) suppression. Subsequently, the FDA approved two changes to the labeling of levothyroxine sodium (Tirosint-SOL, IBSA). The first change was for use in combination with a proton pump inhibitor (PPI). The second adjustment was the timing of levothyroxine sodium administration. The approved labeling changes were based on the results of two clinical studies that found no interaction between levothyroxine sodium and PPIs, and the same results were shown when administered 15 minutes and 30 minutes before breakfast. This led to the approval to label levothyroxine sodium as the only FDA-approved LT4 therapy that does not have label interactions with PPIs and can be taken 15 minutes before breakfast. | [Uses]
One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroid hormone, but has been used to treat hyperlipidemia. | [Definition]
ChEBI: The sodium salt of L-thyoxine. It is used as replacement therapy in the treatment of hypothyroidism. | [Indications]
Levothyroxine sodium (Levothroid, Synthroid, Levoxine)
is the sodium salt of the naturally occurring levorotatory
isomer of T4. It is the preparation of choice for
maintenance of plasma T4 and T3 concentrations for
thyroid hormone replacement therapy in hypothyroid
patients. It is absorbed intact from the gastrointestinal
tract, and its long half-life allows for convenient oncedaily
administration. Since much of the T4 is deiodinated
to T3, it is usually unnecessary to use more expensive
preparations containing both T4 and T3.The aim
is to establish euthyroidism with measured serum concentrations
of T4, T3, and TSH within the normal range.
The TSH-suppressive effects of exogenous T4 also
prove useful in removing the stimulatory effects of TSH
on the thyroid gland in the management of simple
nonendemic goiter, chronic thyroiditis, and TSHdependent
thyroid carcinoma. | [Manufacturing Process]
A 9.30 g portion of N-acetyl-L-diiodotyrosinamide was suspended in 100 ml of
0.05M boric acid (H3BO3) and 100 ml of 95% ethanol, and the solid was
dissolved by adjusting the pH to 10.5 with 2N sodium hydroxide (NaOH). A
15% (by weight) portion of manganese sulfate monohydrate was added and
the solution heated at 44°C under conditions of oxygenation while being
agitated mechanically. After approximately 24 hours of incubation, the
precipitated product was collected and separated from the catalyst, providing
the amide of N-acetyl-L-thyroxine in 30.6% yield. On hydrolysis (removal of
both amide functions), achieved by refluxing in glacial acetic acid-hydrochloric
acid (approximately 2:1), L-thyroxine is obtained. It was isolated as the
sodium salt, containing approximately 5 molecules of water of hydration. | [Brand name]
Levo-T (Alara);
Levolet (Vintage); Levothroid (Lloyd); Levoxyl (Jones);
Novothyrox (Genpharm); Synthroid (Abbott); Unithroid
(Stevens J). | [Therapeutic Function]
Thyroid hormone | [General Description]
Levothyroxine sodium,O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-2-tyrosinemonosodium salt, hydrate (Synthroid, Letter, Levoxine,Levoid), is the sodium salt of the levo isomer of thyroxine,which is an active physiological principle obtained from thethyroid gland of domesticated animals used for food by humans.It is also prepared synthetically. The salt is a light yellow,tasteless, odorless powder. It is hygroscopic but stablein dry air at room temperature. It is soluble in alkali hydroxides,1:275 in alcohol, and 1:500 in water, to give a pH ofabout 8.9. | [Clinical Use]
Liothyronine sodium occurs in vivo together withlevothyroxine sodium; it has the same qualitative activitiesas thyroxine but is more active. It is absorbed readily fromthe gastrointestinal tract, is cleared rapidly from the bloodstream,and is bound more loosely to plasma proteins than isthyroxine, probably because of the less acidic phenolic hydroxylgroup.Its uses are the same as those of levothyroxine sodium,including treatment of metabolic insufficiency, male infertility,and certain gynecological disorders. | [Veterinary Drugs and Treatments]
Levothyroxine sodium is indicated for the treatment of hypothyroidism
in all species. | [References]
[1] Patent: WO2009/136249, 2009, A1. Location in patent: Page/Page column 5
[2] Patent: WO2015/11573, 2015, A1. Location in patent: Page/Page column 7 ;8
[3] Patent: WO2015/151013, 2015, A1. Location in patent: Paragraph 12; 13 |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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